If I try and transfer larger files it says:
29/01/2010 08:26:20: Uploading: Largefile.so
and does nothing else. Clicking back into the server window and typing anything causes the conenction to drop and I have to reconnect.

Btw, thanks for reporting so many bugs in TeSSH. I was planning a Beta release of TeSSH today, so it might be a little late to get the fixes into this beta version, but I'll do my best. But it's really important for me to start getting some good beta testers for TeSSH. So I really appreciate that you took the time to play with TeSSH and report the problems with some of the newer features like the SFTP.